This invention relates to a method for the production of certain novel cyclic compounds which contain selenium or tellurium or both.
The interaction of organic compounds with selenium or tellurium is known generally to result in somewhat unusual compounds which often are complex and polymeric. Typical preparative methods for said compounds require acetylenic compounds, diolefins, difunctional organic compounds, such as dihalides, or combinations of these. For example, U.S. Pat. No. 3,149,101 discloses the reaction between dihalobutadienes and a large class of compounds for form the corresponding heterocyclic dienes, e.g., tetraphenyltellurophene. The multi-step preparation of 1,2,3-triselenacyclopentane from 1,2-dibromoethane is disclosed in Volume 45 of the J. Org. Chem., pp. 2632-6 (1980). The preparation of tellurium-containing heterocyclic compounds, such as cis-3,5-dibenzylidene-1,2,4-tritellurole from sodium phenylethnyltellurolate and ethereal HCl, is described in V. 22 (42) of Tetrahedron Letters, pp. 3199-200 (1981).
U.S. Pat. No. 3,671,467 discloses the reaction of difunctional organic molecules having functional moieties selected from the group consisting of "halides, epoxy and sulfonate ester groups and diazonium halides" with a difunctional reagent containing a diselenide. In particular, Example 1 of said patent discloses contacting sodium sulfite (Na.sub.2 So.sub.3), selenium, water and 4,6-bis(chloromethyl)-m-xylene at reflex temperature to prepare 4,6-bis(methyl)-m-xylene diselenide. Said patent further discloses that the products of the reaction generally described in this paragraph may be polymerized by reacting the products with additional elemental selenium, generally at temperatures of from about 200.degree. C. to about 300.degree. C. U.S. Pat. No. 3,971,742 describes a process which is similar to the process of U.S. Pat. No. 3,671,467 except that mixtures of selenium and tellurium are employed.
U.S. Pat. No. 4,233,131 discloses the production of compound such as ethylene episelenide by irradiating a mixture of elemental selenium and olefins of 2-6 carbon atoms with certain electromagnetic radiation. Thus, said process does not require the acetylenic compounds, etc., of the typical methods described hereinabove for the preparation of selenium- or tellurium-containing organic compounds. However, it does require the use of electromagnetic radiation.
Heretofore, novel 3,4,5-tri(selena- or tellura-)polycyclo compounds, as described hereinafter, and the corresponding polymers have not been prepared. It would be desirable to prepare said polycyclo compounds using a single process which would not require electromagnetic radiation or the acetylenic compounds, etc., of prior art processes.